4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside

Base Information

• Chemical Name: 4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside
• CAS No.: 313054-85-2
• Molecular Formula: C₁₃H₁₃NO₃S₂
• Molecular Weight: 295.383
• Mol file: 313054-85-2.mol

Synonyms:4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside

Chemical Property of 4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside

There total 10 articles about 4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Methanesulfonic acid (2S,3S,4R,5R)-2,5-bis-bromomethyl-4-hydroxy-tetrahydro-furan-3-yl ester (33032-87-0) → 4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside (313054-85-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / p-TsOH / 1 h / 20 °C

2: 50 percent / potassium thiobenzoate / 4 h / Heating

3: 63 percent / dimethylformamide / 5 h / 100 °C

4: Dowex 50 WX₂ (H+) / 3 h / 20 °C

5: pyridine / 3 h / 20 °C

6: NCS / toluene / 1 h / 20 °C

7: ZnO / acetonitrile / 0.5 h / 20 °C

8: 75 percent / NaOMe / methanol / 2 h / 20 °C

With pyridine; N-chloro-succinimide; thiobenzoic acid potassium salt; Dowex 50 WX₂ (H+); sodium methylate; toluene-4-sulfonic acid; zinc(II) oxide; In methanol; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Etherification / 2: Cyclization / 3: Substitution / 4: Hydrolysis / 5: Acetylation / 6: Substitution / 7: Substitution / 8: Hydrolysis;

DOI:10.1016/S0008-6215(00)00156-7

Reference yield:

Acetic acid (1R,5S,6S,7S)-7-hydroxy-8-oxa-3-thia-bicyclo[3.2.1]oct-6-yl ester → 4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside (313054-85-2)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 3 h / 20 °C

2: NCS / toluene / 1 h / 20 °C

3: ZnO / acetonitrile / 0.5 h / 20 °C

4: 75 percent / NaOMe / methanol / 2 h / 20 °C

With pyridine; N-chloro-succinimide; sodium methylate; zinc(II) oxide; In methanol; toluene; acetonitrile; 1: Acetylation / 2: Substitution / 3: Substitution / 4: Hydrolysis;

DOI:10.1016/S0008-6215(00)00156-7

Reference yield:

3,4-di-O-acetyl-1,6:2,5-dianhydro-1-thio-D-glucitol (55174-77-1) → 4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside (313054-85-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NCS / toluene / 1 h / 20 °C

2: ZnO / acetonitrile / 0.5 h / 20 °C

3: 75 percent / NaOMe / methanol / 2 h / 20 °C

With N-chloro-succinimide; sodium methylate; zinc(II) oxide; In methanol; toluene; acetonitrile; 1: Substitution / 2: Substitution / 3: Hydrolysis;

DOI:10.1016/S0008-6215(00)00156-7

upstream raw materials:

Methanesulfonic acid (2S,3S,4R,5R)-2,5-bis-bromomethyl-4-hydroxy-tetrahydro-furan-3-yl ester

4-cyanobenzenethiol

3,4-di-O-acetyl-1,6:2,5-dianhydro-1-thio-D-glucitol

1,3,4-tri-O-acetyl-2,5-anhydro-6-thio-α-L-guloseptanose

Downstream raw materials:

4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside (1R)-S-oxide

4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside (1S)-S-oxide